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TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE

Basic information Uses Safety Supplier Related

TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE Basic information

Product Name:
TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE
Synonyms:
  • TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE
  • 2-(Boc-amino)-4-bromopyridine
  • tert-butyl N-(4-broMopyridin-2-yl)carbaMate
  • CarbaMicacid,N-(4-broMo-2-pyridinyl)-,1,1-diMethylethylester
  • tert-Butyl N-(4-bromo-2-pyridyl)carbamate
  • t-Butyl 4-bromopyridin-2-ylcarbamate
  • (4-Bromo-pyridin-2-yl)-carbamic acid tert-butyl ester
  • ert-butylN-(4-bromopyridin-2-yl)carbamate
CAS:
207799-10-8
MF:
C10H13BrN2O2
MW:
273.13
EINECS:
817-281-8
Product Categories:
  • Halides
  • Pyridines
Mol File:
207799-10-8.mol
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TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE Chemical Properties

Boiling point:
296.7±25.0 °C(Predicted)
Density 
1.453±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
pka
11.89±0.70(Predicted)
Appearance
White to light brown Solid
InChI
InChI=1S/C10H13BrN2O2/c1-10(2,3)15-9(14)13-8-6-7(11)4-5-12-8/h4-6H,1-3H3,(H,12,13,14)
InChIKey
IRRRVCLDPODLJG-UHFFFAOYSA-N
SMILES
C(OC(C)(C)C)(=O)NC1=NC=CC(Br)=C1
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Safety Information

HS Code 
2933399990
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TERT-BUTYL 4-BROMOPYRIDIN-2-YLCARBAMATE Usage And Synthesis

Uses

tert-butyl (4-bromopyrimidin-2-yl)carbamate can be used as a pharmaceutical synthesis intermediate.

Synthesis

84249-14-9

24424-99-5

207799-10-8

General procedure for the synthesis of 2-Boc amine-4-bromopyridine from 2-amino-4-bromopyridine and di-tert-butyl dicarbonate: To a solution of 4-bromopyridin-2-amine (519 mg) in anhydrous THF (15 mL) was slowly added bis(trimethylmethylsilyl)amide (1 M solution in hexane, 6 mL) at -5 °C and the reaction mixture was stirred. After maintaining this temperature for 10 minutes, di-tert-butyl dicarbonate (654 mg) was added and the reaction mixture was transferred to room temperature to continue stirring for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of saturated ammonium chloride solution (20 mL) and the mixture was extracted with EtOAc. The organic layers were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to afford the target product 2-Boc amine-4-bromopyridine in 96% yield.

References

[1] Patent: US2014/194443, 2014, A1. Location in patent: Paragraph 0541-0542
[2] Patent: WO2014/108337, 2014, A1. Location in patent: Page/Page column 69
[3] Patent: WO2016/124508, 2016, A1. Location in patent: Page/Page column 39
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637
[5] Patent: CN104744433, 2016, B. Location in patent: Paragraph 0027; 0028

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